Formaldehyde → HCID 66906071, compound

HRID 1690842Notes

Reaction equation

HRID 1690842 reaction equation
[OH-:1].C[N+:3]([CH3:6])(C)C.[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]#N.C=O>O1CCCC1>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]([CH2:15][OH:1])[C:6]#[N:3]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 60966Tetramethylammonium hydroxideHCID 76112(o-Chlorophenyl)acetonitrile

Product 1

HCID 66906071HCID 66906071, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 330 μL sample of tetramethylammonium hydroxide (40% in water) was added with stirring to a solution of 750 mg (4.95 mmol) of 2-chlorophenylacetonitrile and 1.86 mL of 37% formaldehyde in 9 mL of tetrahydrofuran. The reaction was quenched at 12 min by acidification with 3 N HCl and diluted with ethyl acetate and water. The organic phase was washed with water, saturated salt solution, then stripped to an oil. This was flash chromatographed on 15 g of silica gel eluting with 5→90% ethanol in hexane. Fractions containing product were stripped to yield 622 mg (69%) of the alcohol as a colorless oil, Rf 0.14 (silica gel, ethyl acetate:hexane=1:4).

Workup

  1. customThe reaction was quenched at 12 min by acidification with 3 N HCl
  2. additiondiluted with ethyl acetate and water
  3. washThe organic phase was washed with water, saturated salt solution
  4. customThis was flash chromatographed on 15 g of silica gel eluting with 5→90% ethanol in hexane
  5. additionFractions containing product

Sources & evidence

ORD record
ord-966d46301c53495fb257b5cd0ad65a7e
Source dataset
uspto-grants-2012_04
Patent number
US08153688B2

Reaction notes

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